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Chapter 14: Q25P (page 737)

Question. Propose a complete mechanism for the reaction of cyclopentene oxide with sodium methoxide in methanol.

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01

Attack of methoxide ion as nucleophile on cyclopentene oxide:

Methoxide ion acts as a good nucleophile and attacks at the epoxide ring as epoxide is strained due to presence of angle strain and attack of nucleophile opens up epoxide ring and release strain. Methoxide ion attacks from opposite plane of epoxide as epoxide is formed above the plane, so attack of methoxide ion will be from below the plane.

Attack of methoxide ion as nucleophile

02

Formation of the product:

After ring opening of epoxide, oxygen acquires negative charge and acts as good base and abstracts proton from methanol which leads to the formation of required product and methoxide ion is formed as side product.

Formation of product

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Most popular questions from this chapter

Show the rest of the mechanism for formation of cyclized intermediate in figure 14-6.

Role of squalene in the biosynthesis of steroids. The biosynthesis of steroids starts with epoxidation of squalene to squalene-2,3-epoxide. The opening of this epoxide promotes cyclization of the carbon skeleton under the control of an enzyme. The cyclized intermediate is converted to lanosterol and then to other steroids.

Question. (A true story.) An inexperienced graduate student moved into a laboratory and began work. He needed some diethyl ether for a reaction, so he opened an old, rusty 1-gallon can marked 鈥渆thyl ether鈥� and found there was half a gallon left. To purify the ether, the student set up a distillation apparatus, started a careful distillation, and went to the stockroom for the other reagents he needed. While he was at the stockroom, the student heard a muffled 鈥渂oom鈥�. He quickly returned to his lab to find a worker from another laboratory putting out a fire. Most of the distillation apparatus was embedded in the ceiling.

(a) Explain what probably happened.

(b) Explain how this near disaster might have been prevented.

Propose a Williamson synthesis of 3-butoxy-1,1-dimethylcyclohexane from 3,3-dimethyl-cyclohexanol and butan-1-ol.

(a) Tetramethyloxirane is too hindered to undergo nucleophilic substitution by the hindered alkoxide, potassium tert-butoxide. Instead, the product is the allylic alcohol shown. Propose a mechanism to explain this reaction. What type of mechanism does it follow?

(b) Under mild acid catalysis, 1,1-diphenyloxirane undergoes a smooth conversion to diphenylethanal (diphenylacetaldehyde). Propose a mechanism for this reaction. (Hint: Think Pinacol.)

Question. Propose a mechanism for the following reaction.
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